momandboys's Blog

I loved women. A lot. My obsession with women later became a desire to wear women clothing. One day, three months after my 18th birthday, I could not hold back any longer, and I put on the the most accessible lingerie I could find - that of my mother.

Since then, I frequently visited my mom's wardrobe whenever she was out. I would wear her clothes, and it would make me feel sexy. I would pretend I am a woman, and take sexy pictures of myself. I realized how much I liked this, and this led to me realizing my bisexuality. I wanted a man to make me his woman.

I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever seen complete with calf length stockings and a garter belt. I wasted no time stripping off and sliding on the sexy underwear, next I found her makeup bag and applied some red lipstick and black mascara. that was when I heard the front door open, my mum was home early!! I tried to hide but before I could she strode int... Continue»

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.

It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s oldest and most respected law firms. Mark recalled bitterly that his parents got along fine until she... Continue»

My parents had one c***d, a boy, me. Many times I overheard them talking about me and how they wished I was a girl. I always felt a twinge of pain when I heard them say that but they loved me, always treated me very well and never said anything to my face so I pretty much ignored it. When I think back maybe dad’s parents felt the same way since he was an only c***d also. In retrospect it would explain dad’s secret hobby, as he and mom called it. It was a secret, or so mom and he thought but I knew about it. I had discovered it when I was about four. One night back then I got up in the middle o... Continue»

Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house- mansion, really- a few doors down. Billy Cravitz, Sam's nemesis, and the rest of the neighborhood gang had given Sam an ultimatum: break into Ms. Johnson's house or be an outcast for the entire summer. Sam knew it was stupid to go along, but he knew his reputation ... Continue»

My name is now Stephanie, once it was Stephen. I would like to relate how I was turned into a girl (really a transvestite slave) by the beautiful young lady who has become my mistress. I have always felt that I should have been born a female. I definitely have female traits. I have a very feminine voice and I cry over the silliest things. Just like a woman would.

Cindy's dominance over me has expanded my submissive nature. I love Mistress Cindy and happily submit to her every desire. In high school, I spent two frustrating years trying to date the opposite sex. I found girls to be rather di... Continue»

I had come home early from work and found my son, Jamie, sitting at my vanity, putting on make-up. He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie. He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick. He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he had done this many times before.

Of course, Jamie was very upset and embarrassed when I announc... Continue»

It's true that I had become accustomed to drama in my f****y. My father was loud and mean, especially when he was d***k, which was most evenings and every weekend. He would back my poor mother into a corner of the kitchen and berate her, towering over her in that threatening way that I knew so well, telling her she was fat and ugly and stupid and spending too much money on me. He would get louder and louder until she finally began to tremble and sob – then he would storm out of the house in disgust, as if her crying gave him the right to leave his "silly emotional wife" and visit his drinking ... Continue»

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I’d said something to offend him and responded by saying, “Well, no one’s ever told me that I was unattractive.” When I suggested that was because no one had had the occasion to be brutally honest with him, he got visibly pissed off and blurted out, “Well, my mom thinks . . .” and caught h... Continue»

They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car.

It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. Im very easily intimidated. And there I was in a tiny plaid mini and white pump sandals about to mince my way passed a group of young black street-toughs. Even in broad daylight, even in guy-clothes, I'd have been terrified…

Since posting the story about how my aunt introduced me to makeup and crossdressing, I've decided to tell the story about my uncle. He was a man's man with the most beautiful cock I've still ever seen in person. Anyway, me and my cousin used to play with his mother's makeup and wore her lingerie while we jacked off and sucked each other's cock. We did this almost every day in the summer months from the time we were around 11 until we both were almost 16. It was great fun and we had many orgasms together.

My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in her 3 inch heels. She had long auburn hair with beautiful waves in it. She wore a 9 1/2 shoe. Her hands and feet were large, but so sexy looking with nail polish on. Her blue eyes would melt you. She had a great mirrored vanity she would sit at for hours and try different combinations of makeup. Sh... Continue»

You know those words that just have so much impact on you they just shut you up and keep you thinking for the rest of the day? There have been other instances in my life that have done this to me, all of them done by my mother. The first time when I was a c***d she asked me if I had tried on her pantyhose in the bathroom. This was true because after I had my fun with them I placed them in the hamper. That was one of the very first times I had ever worn female clothing. Naturally being a little k** I didn't know how to react to the situation so I got angry and basically over reacted saying thin... Continue»

I have always loved the feeling of something lacy or sexy on my body. I call it a passion of some sorts, wearing these things made me feel very special and desirable. I was raised by my mom and the closest f****y we had was my Aunt Trish and her two daughters. To start my collection of these things to wear, I would take things they left lying around the house and later claimed as my own since I assumed they were things that were lost. My mom was always working or going to my aunt's house on the beach for the weekend. I never was a problem k** and always made good grades in school. Mom never re... Continue»

I moved away from home when I was 18. My dad and I hated each other. He was jealous of how my mother treated me. It was nothing for her to come in my shower just wearing a bra and sexy panties and wash my whole body, cock and all. She would give me a body rub down once a week, I lived for that.

Mom would come in my room wearing just a bra and panties, climb on my back rubbing and caressing my back and my ass. Then I would turn over, many times mom sat right on my cock while she rubbed my chest. My cock is great, 10 thick inches, "It's a woman pleaser," my Mom told me one night.

That's not an excuse for what I've become – and that's not to say I need an excuse – it's just a simple fact that some people find relevant when trying to examine what I've become.

Anyway, he was killed in a plane crash before I was born. Technically, he was killed in a plane crash while I was being born, but he died without knowing that. He'd been overseas at a business conference when my mom called to tell him she was going into labor, and had boarded the first plane he could back to North America. Ironically, it wasn't that long, turbulent, twenty hour flight that... Continue»

My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is involved.

I have to admit that I have always been bothered by my penis size. I've seen smaller dicks online by typing 'small penis' in google but mine is defiantly nothing to boost about at around five inches. I worry that girls are gonna laugh at me, which would be mean, or that I just won't be able to get t... Continue»

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.
I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use it. It could be fun reading about it a year after. It does look like a girl’s diary. Maybe boys don... Continue»